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Michael addition reactions of cyclanones with acrylamides: Producing 2-carbamoylethyl derivatives or ene-lactams

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Abstract

The electron-withdrawing groups (EWGs) in the electrophilic alkenes employed in the Michael addition reaction are almost only CO2R, CN, COR, NO2, and SO2Ph. Although amides (CONR1R2) are also typical electron-withdrawing groups and are of great importance in organic synthesis, they are scarcely employed as the EWGs of the electrophilic alkenes in the Michael addition reaction. In this work, the Michael reactions of acrylamide and its derivatives with cyclanones were successfully carried out in the presence of enough radical inhibitors. The amide groups play a key role in producing the preferred products. The N-substituted acrylamides, including N-monosubstituted and N,N-disubstituted acrylamides could react with cyclohexanone (CHn) to give the expected 2-carbamoylethyl derivatives; however, acrylamide reacting with cyclohexanone only produced ene-lactam. Cyclanones also have effects on the products, while the ring size of cyclanones influences the reaction yield and the α-substituent decides the ratio of resulting isomeric ene-lactams.

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Authors and Affiliations

  1. Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai, 200237, China

    WeiFeng Dai, ChaoHua Wang, Xi Zhang, JinMing Zhang & MeiDong Lang

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  1. WeiFeng Dai
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  2. ChaoHua Wang
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  3. Xi Zhang
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  4. JinMing Zhang
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  5. MeiDong Lang
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Correspondence to MeiDong Lang.

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Supported by the National Natural Science Foundation of China (Grant Nos. 20374013 and 20674019), Program for New Century Excellent Talents in University (Grant No. NCET-04-0413), Science and Technology Commission of Shanghai Municipality (Grant Nos. 03JC14023 and 05DJ14005), “Shu Guang” Project of Shanghai Municipal Education Commission and Specialized Research Fund for the Doctoral Program of Higher Education (Grant No.20060251015)

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Dai, W., Wang, C., Zhang, X. et al. Michael addition reactions of cyclanones with acrylamides: Producing 2-carbamoylethyl derivatives or ene-lactams. Sci. China Ser. B-Chem. 51, 1044–1050 (2008). https://doi.org/10.1007/s11426-008-0095-3

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  • DOI: https://doi.org/10.1007/s11426-008-0095-3

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